6-aminohexanoic acid

• ChemBase ID: 395
• Molecular Formular: C6H13NO2
• Molecular Mass: 131.17292
• Monoisotopic Mass: 131.09462866
• SMILES: OC(=O)CCCCCN
• Canonical SMILES: NCCCCCC(=O)O
• InChI: InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
• InChIKey: SLXKOJJOQWFEFD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-aminohexanoic acid
• IUPAC Traditional name: 6-amino hexanoic acid; aminocaproic acid
• Brand Name: Acepramin; Acepramine; Afibrin; Amicar; Amikar; Aminokapron; Atsemin; Caplamin; Capracid; Capramol; Capranol; Caprocid; Caprolisin; EACA; EACS; Epsamon; Epsicapron; Epsikapron; Epsilcapramin; Epsilcapramine; Hemocaprol; Hemopar; Hepin; Ipsilon; Respramin
• Synonyms: Aminocaproate; ACS; Aminocaproic; aminocaproic acid; ε-amino caproic acid; ε-Ahx; 6-aminohexanoic acid; E-aminocaproic acid; Aminocaproic Acid; 6-Amino-n-hexanoic acid; 6-Aminocaproic acid; EACA; ε-AMINO-n-CAPROIC ACID; ε-Aminocaproic acid; 6-Aminohexanoic acid solution; Additive Screening Solution 32/Fluka kit no 78374; 6-Aminohexanoic acid; A 14719; Acepramin; Acepramine; Acikaprin; Afibrin; Amikar; Aminokapron; CL 10304; CY 116; Caplamin; Capramol; Caprocid; Caprolisin; EACS; Epsamon; Epsicapron; Epsikapron; Epsilcapramin; Epsilon S; Hemocaprol; Hemopar; Hepin; Ipsilon; NSC 212532; NSC 26154; NSC 400230; Respramin; ε-Amino-n-caproic Acid; ε-Amino-n-hexanoic Acid; ε-Aminohexanoic Acid; ε-Leucine; ε-Norleucine; ω-Aminocaproic Acid; ω-Aminohexanoic Acid; 6-Aminohexanoic Acid; 6-Aminocaproic acid; Amicar; 6-Amino Hexanoic Acid; epsilon-Aminocaproic acid; 6-氨基己酸; 6-氨己酸; ε-氨基己酸; 6-氨己酸; 6-氨基己酸

Database IDs

• CAS Number: 60-32-2
• EC Number: 200-469-3
• MDL Number: MFCD00008238
• Beilstein Number: 906872
• Merck Index: 14432
• PubChem SID: 46508972; 160963858; 24890662; 46506934; 24278238
• PubChem CID: 564

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.72614
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.050338
• LogD (pH = 7.4): -1.9963912
• Log P: -1.9971552
• Molar Refractivity: 34.6598 cm^3
• Polarizability: 13.835553 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.69
• LOG S: -0.46
• Solubility (Water): 4.52e+01 g/l

PROPERTIES

Physical Property

• Solubility: 5.05E+005 mg/L; H2O: soluble0.5 M, clear; H2O: soluble50 mg/mL; Water
• Apperance: white powder; White Solid
• Melting Point: 203-205°C; 204-206; 207-209 °C (dec.)(lit.); 210-212°C
• Density: 1.03 g/mL at 20 °C
• Hydrophobicity(logP): 0; -2.235

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: MO6300000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... PLG(5340); human ... PLG(5340)rat ... Ppm1a(24666)

Product Information

• Purity: ≥98.5% (NT); ≥99%; ≥99% (titration); ≥99.0% g/mL; 95%; 98%; 99%
• Concentration: 1 M
• Grade: puriss.; SAJ special grade
• Salt Data: Free Base
• Packaging: vial of 200 mg
• Ignition Residue: ≤0.1%
• Impurities: ≤0.005% Phosphorus (P); ≤0.1% Insoluble matter
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.005%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.001%; Na: ≤0.02%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• Antion Traces: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• Linear Formula: H2N(CH2)5CO2H

DETAILS

MP Biomedicals - 02101645

Crystalline
A plasmin inhibitor.

DrugBank - DB00513

• Drug Groups: approved; investigational
• Description: An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties. [PubChem]
• Indication: For use in the treatment of excessive postoperative bleeding.
• Pharmacology: Aminocaproic acid works as an antifibrinolytic. It is a derivative of the amino acid lysine. The fibrinolysis-inhibitory effects of aminocaproic acid appear to be exerted principally via inhibition of plasminogen activators and to a lesser degree through antiplasmin activity. Aminocaproic acid may be a possible prophylactic for vascular disease, as it may prevent formation of lipoprotein (a), a risk factor for vascular disease.
• Toxicity: A few cases of acute overdosage with intravenous administration have been reported. The effects have ranged from no reaction to transient hypotension to severe acute renal failure leading to death. The intravenous and oral LD₅₀ were 3.0 and 12.0 g/kg respectively in the mouse and 3.2 and 16.4 g/kg respectively in the rat. An intravenous infusion dose of 2.3 g/kg was lethal in the dog.
• Affected Organisms: Humans and other mammals
• Biotransformation: Sixty-five percent of the dose is recovered in the urine as unchanged drug and 11% of the dose appears as the metabolite adipic acid.
• Absorption: Absorbed rapidly following oral administration. In adults, oral absorption appears to be a zero-order process with an absorption rate of 5.2 g/hr. The mean lag time in absorption is 10 minutes. After a single oral dose of 5 g, absorption was complete (F=1).
• Half Life: The terminal elimination half-life is approximately 2 hours.
• Elimination: Renal excretion is the primary route of elimination, whether aminocaproic acid is administered orally or intravenously.
• Distribution: * 23.1 ± 6.6 L
• Clearance: * 169 mL/min
• External Links: Wikipedia; RxList; Drugs.com

DrugBank - DB04134

• Drug Groups: experimental
• Description: An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties. [PubChem]

Selleck Chemicals - S1671

Research Area: Cardiovascular Disease
Biological Activity:
Aminocaproic acid(Amicar) is a derivative and analogue of the amino acid lysine, which makes it an effective inhibitor for enzymes that binds particular residue. Such enzymes include proteolytic enzymes like plasmin, the enzyme is responsible for fibrinolysis. For this reason it is effective in treatment of certain bleeding disorders, especially fibrogenemia, and is marketed as Amicar. Aminocaproic acid is also an intermediate in the polymerization of Nylon-6, where it is formed by ring-opening hydrolysis of caprolactam. [1]

Sigma Aldrich - A2504

包装
1 kg in poly bottle
25, 100, 500 g in poly bottle
5 kg in poly drum
Application
EACA is directly soluble in water at 25 mg/ml. As an inhibitor of plasmin it is has been utilized in the clotting buffer for fibrinogen assays. This buffer is 10 mM potassium and sodium phosphate, pH 6.4, with 0.20 g CaCl2, 5 g 6-Aminohexanoic acid, 1 g sodium azide, and 9 g NaCl in 1 liter. The buffer is stable indefinitely at room temperature.
Biochem/physiol Actions
EACA is reported to inhibit chymotrypsin, Factor VIIa, lysine carbo-xy-peptidase, plasmin, and plasminogen activator.
赖氨酸类似物。促进纤溶酶快速解离，从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。据报告，EACA 可抑制纤溶酶原结合至活化的血小板。早期报告表明，EACA 可抑制补体系统第一组分的活化。结合并灭活羧肽酶 B。

Sigma Aldrich - A7824

Biochem/physiol Actions
赖氨酸类似物。促进纤溶酶快速解离，从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。1,2据报告，EACA 可抑制纤溶酶原结合至活化的血小板。3早期报告表明，EACA 可抑制补体系统第一组分的活化。4结合并灭活羧肽酶 B。5

Sigma Aldrich - A9812

包装
棕色螺纹盖样品瓶包装
Biochem/physiol Actions
赖氨酸类似物。促进纤溶酶快速解离，从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。1,2据报告，EACA 可抑制纤溶酶原结合至活化的血小板。3早期报告表明，EACA 可抑制补体系统第一组分的活化。4结合并灭活羧肽酶 B。5

Sigma Aldrich - A44606

Application
Hemostat.2,6 Used as a lysine analogue to characterize binding sites in plasminogen.7,8
Biochem/physiol Actions
Lysine analog. Promotes rapid dissociation of plasmin, thereby inhibiting the activation of plasminogen and subsequent fibrinolysis.1,2 Reported to inhibit plasminogen binding to activated platelets.3 An early report indicated that it inhibits the activation of the first component of the complement system.4 Binds and inactivates Carboxypeptidase B.5

Sigma Aldrich - 07260

Other Notes
Improves solubilization of membrane proteins in electrophoresis6
Biochem/physiol Actions
Lysine analog. Promotes rapid dissociation of plasmin, thereby inhibiting the activation of plasminogen and subsequent fibrinolysis.1,2 Reported to inhibit plasminogen binding to activated platelets.3 An early report indicated that it inhibits the activation of the first component of the complement system.4 Binds and inactivates Carboxypeptidase B.5

Sigma Aldrich - 01-3540

Biochem/physiol Actions
Lysine analog. Promotes rapid dissociation of plasmin, thereby inhibiting the activation of plasminogen and subsequent fibrinolysis.1,2 Reported to inhibit plasminogen binding to activated platelets.3 An early report indicated that it inhibits the activation of the first component of the complement system.4 Binds and inactivates Carboxypeptidase B.5

Toronto Research Chemicals - A609985

6-Aminohexanoic Acid is a reagent commonly used for the extraction of aldehydes from reaction mixtures. 6-Aminohexanoic Acid has also been shown to improve solubilization of membrane proteins in electrophoresis. Studies suggest that 6-Aminohexanoic Acid i

REFERENCES

• Steffen, L.W., and Steffen, B.W., Clin. Chem. , 22 : 381, (1976).
• http://en.wikipedia.org/wiki/Aminocaproic_acid
• Ohta ,S. et al.: Chem. Pharm. Bull., 28, 1917 (1980)
• Shagger, H. et al.: Anal. Biochem., 199, 223 (1980)
• Soter, N.A. et al.: J. Immunol., 114, 928 (1980)
• Has been recommended as a reagent for the extraction of aldehydes from reaction mixtures, giving better recovery than bisulfite: Chem. Pharm. Bull., 28, 1917 (1980).